CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Australian Journal of Chemistry   
Australian Journal of Chemistry
Journal Banner
  An international journal for chemical science
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Structure
Contacts
For Advertisers
Content
Online Early
Current Issue
Just Accepted
All Issues
Virtual Issues
Special Issues
Research Fronts
Sample Issue
Covers
For Authors
General Information
Scope
Submit Article
Author Instructions
Open Access
For Referees
Referee Guidelines
Review an Article
For Subscribers
Subscription Prices
Customer Service
Print Publication Dates

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook twitter LinkedIn

Affiliated with RACI

Royal Australian Chemical Institute
Royal Australian
Chemical Institute


 

Article << Previous     |     Next >>   Contents Vol 66(1)

Solid-Phase Organic Synthesis of Dexoxadrol Analogues

Michael Sax A and Bernhard Wünsch A B

A Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhems-Universität Münster, Hittorfstrasse 58-62, D-48149 Münster, Germany.
B Correpsonding author. Email: wuensch@uni-muenster.de

Australian Journal of Chemistry 66(1) 93-97 http://dx.doi.org/10.1071/CH12356
Submitted: 28 July 2012  Accepted: 4 September 2012   Published: 22 October 2012


 
 Full Text
 PDF (411 KB)
 Export Citation
 Print
  
Abstract

A solid-phase synthesis of dexoxadrol analogues like-13 and unlike-13 bearing an oxo group in the 4-position of the piperidine ring has been developed using aminomethyl substituted polystyrene resin as solid support. The synthesis comprises a hetero-Diels–Alder reaction of imine 7b with Danishefsky’s diene 8 in the presence of the Lewis acid Yb(OTf)3 and a conjugate reduction of the double bond of 9b with LiBHEt3 and BF3. The cleavage of the product from the solid support was performed with 1-chloroethyl chloroformate. All transformations on the solid support and additionally the cleavage reaction had to be compatible with the large and acid labile acetalic 1,3-dioxolane moiety in 2-position of the piperidine ring. The oxodexoxadrol derivative 12 was obtained in an overall yield of 17 %.





References

[1]  W. R. Hardie, J. Hidalgo, I. F. Halverstadt, R. E. Allen, J. Med. Chem. 1966, 9, 127.
         | CrossRef | CAS |

[2]  A. Thurkauf, P. C. Zenk, R. L. Balster, E. L. May, C. George, F. I. Carroll, S. W. Mascarella, K. C. Rice, A. E. Jacobson, M. V. Mattson, J. Med. Chem. 1988, 31, 2257.
         | CrossRef | CAS |

[3]  J. Hidalgo, C. R. Thompson, Arch. Int. Pharmacodyn. 1965, 153, 105.
         | CAS |

[4]  A. H. Tang, J. D. Kirch, Anesth. Analg. 1973, 52, 577.
         | CrossRef | CAS |

[5]  L. Lasagna, J. W. Pearson, Proc. Soc. Exp. Biol. Med. 1965, 118, 352.
         | CAS |

[6]  M. W Williams, E. A. Williford, C. S. Williams, J. C. Towne, Arch. Int. Pharmacodyn 1969, 178, 26.
         | CAS |

[7]  E. C. Kast, Int. J. Neuropsychiatry 1967, 3, 15.
         | CAS |

[8]  E. L. Frederickson, D. E. Longnecker, G. W. Allen, Anesth. Analg. 1976, 55, 335.
         | CAS |

[9]  L. G. Mendelsohn, G. A. Kerchner, V. Katra, D. H. Zimmermann, J. D. Leander, Biochem. Pharmacol. 1984, 33, 3529.
         | CrossRef | CAS |

[10]  A. E. Jacobson, E. A. Harrison, M. V. Mattson, M. F. Rafferty, K. C. Rice, J. H. Woods, G. Winger, R. E. Solomon, R. A. Lessor, J. V. Silverton, J. Pharmacol. Exp. Ther. 1987, 243, 110.
         | CAS |

[11]  M. Sax, B. Wünsch, Curr. Top. Med. Chem. 2006, 6, 723.
         | CrossRef | CAS |

[12]  M. Sax, K. Ebert, D. Schepmann, B. Wibbeling, B. Wünsch, Bioorg. Med. Chem. 2006, 14, 5955.
         | CrossRef | CAS |

[13]  M. Sax, R. Fröhlich, D. Schepmann, B. Wünsch, Eur. J. Org. Chem. 2008, 6015.
         | CrossRef | CAS |

[14]  A. Banerjee, R. Fröhlich, D. Schepmann, B. Wünsch, Med. Chem. Comm. 2010, 1, 87.
         | CrossRef | CAS |

[15]  A. Banerjee, D. Schepmann, B. Wünsch, Bioorg. Med. Chem. 2010, 18, 4095.
         | CrossRef | CAS |

[16]  A. Banerjee, D. Schepmann, J. Köhler, E.-U. Würthwein, B. Wünsch, Bioorg. Med. Chem. 2010, 18, 7855.
         | CrossRef | CAS |

[17]  W. K. Hagmann, J. Med. Chem. 2008, 51, 4359.
         | CrossRef | CAS |

[18]  S. Nara, R. Tanaka, J. Eishima, M. Hara, Y. Takahashi, S. Otaki, R. J. Foglesong, P. F. Hughes, S. Turkington, Y. Kanda, J. Med. Chem. 2003, 46, 2467.
         | CrossRef | CAS |

[19]  H. Bhagwatheeswaran, S.P. Gaur, P.C. Jain, Synth. Comm. 1976, 615.
         | CAS |

[20]  A. Barco, S. Benetti, C. De Risi, P. Marchetti, G. P. Pollini, V. Zanirato, Tetrahedron Lett. 1998, 39, 1973.
         | CrossRef | CAS |

[21]  K. A. Jørgensen, Angew. Chem. 2000, 112, 3702.
         | CrossRef |

[22]  P. Buonora, J.-C. Olsen, T. Oh, Tetrahedron 2001, 57, 6099.
         | CrossRef | CAS |

[23]  A. Barco, S. Benetti, C. De Risi, P. Marchetti, G. P. Pollini, V. Zanirato, Tetrahedron Lett. 1998, 39, 7591.
         | CrossRef | CAS |

[24]  Y. Wang, S. R. Wilson, Tetrahedron Lett. 1997, 38, 4021.
         | CrossRef | CAS |

[25]  C. Chen, I. A. McDonald, B. Munoz, Tetrahedron Lett. 1998, 39, 217.
         | CrossRef | CAS |

[26]  M. Sax, S. Berning, B. Wünsch, Tetrahedron 2005, 61, 205.
         | CrossRef | CAS |

[27]  A. J. Mancuso, D. Swern, Synthesis 1981, 165.
         | CrossRef | CAS |

[28]  L. Hansson, R. Carlson, Acta Chem. Scand. 1989, 43, 188.
         | CrossRef | CAS |

[29]  J. Barluenga, C. Mateos, F. Aznar, C. Valdés, Org. Lett. 2002, 4, 3667.
         | CrossRef | CAS |

[30]  J. Barluenga, C. Mateos, F. Aznar, C. Valdés, Org. Lett. 2002, 4, 1971.
         | CrossRef | CAS |

[31]  W. Zhang, W. Xie, J. Fang, P. G. Wang, Tetrahedron Lett. 1999, 40, 7929.
         | CrossRef | CAS |

[32]  R. A. Olofson, J. T. Martz, J. P. Senet, M. Piteau, T. Malfront, J. Org. Chem. 1984, 49, 2081.
         | CrossRef | CAS |

[33]  R. A. Olofson, Pure Appl. Chem. 1988, 60, 1715.
         | CrossRef | CAS |

[34]  P. Conti, D. Demont, J. Cals, H. C. J. Ottenheijm, D. Leysen, Tetrahedron Lett. 1997, 38, 2915.
         | CrossRef | CAS |


   
 


    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2015